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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:44 UTC
HMDB IDHMDB0014757
Secondary Accession Numbers
  • HMDB14757
Metabolite Identification
Common NameImatinib
DescriptionImatinib is a drug used to treat certain types of cancer. It is currently marketed by Novartis as Gleevec (USA) or Glivec (Europe/Australia) as its mesylate salt, imatinib mesilate (INN). It is occasionally referred to as CGP57148B or STI571 (especially in older publications). It is used in treating chronic myelogenous leukemia (CML), gastrointestinal stromal tumors (GISTs) and a number of other malignancies. It is the first member of a new class of agents that act by inhibiting particular tyrosine kinase enzymes, instead of non-specifically inhibiting rapidly dividing cells.
Structure
Data?1582753217
Synonyms
ValueSource
4-(4-METHYL-piperazin-1-ylmethyl)-N-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-benzamideChEBI
alpha-(4-Methyl-1-piperazinyl)-3'-((4-(3-pyridyl)-2-pyrimidinyl)amino)-p-toluidideChEBI
STI 571ChEBI
GlamoxKegg
a-(4-Methyl-1-piperazinyl)-3'-((4-(3-pyridyl)-2-pyrimidinyl)amino)-p-toluidideGenerator
Α-(4-methyl-1-piperazinyl)-3'-((4-(3-pyridyl)-2-pyrimidinyl)amino)-p-toluidideGenerator
Imatinib methansulfonateHMDB
STI-571HMDB
GlivecHMDB
Methanesulfonate, imatinibHMDB
Imatinib methanesulfonateHMDB
Imatinib mesylateHMDB
GleevecHMDB
Mesylate, imatinibHMDB
alpha-(4-Methyl-1-piperazinyl)-3'-((4-(3-pyridyl)-2-pyrimidinyl)amino)-p-tolu-p-toluidideHMDB
Chemical FormulaC29H31N7O
Average Molecular Weight493.6027
Monoisotopic Molecular Weight493.259008649
IUPAC NameN-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)-4-[(4-methylpiperazin-1-yl)methyl]benzamide
Traditional Nameimatinib
CAS Registry Number152459-95-5
SMILES
CN1CCN(CC2=CC=C(C=C2)C(=O)NC2=CC(NC3=NC=CC(=N3)C3=CN=CC=C3)=C(C)C=C2)CC1
InChI Identifier
InChI=1S/C29H31N7O/c1-21-5-10-25(18-27(21)34-29-31-13-11-26(33-29)24-4-3-12-30-19-24)32-28(37)23-8-6-22(7-9-23)20-36-16-14-35(2)15-17-36/h3-13,18-19H,14-17,20H2,1-2H3,(H,32,37)(H,31,33,34)
InChI KeyKTUFNOKKBVMGRW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as oxazolidinediones. Oxazolidinediones are compounds containing an oxazolidine ring which bears two ketones.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzolidines
Sub ClassOxazolidines
Direct ParentOxazolidinediones
Alternative Parents
Substituents
  • Oxazolidinedione
  • Dicarboximide
  • Carbamic acid ester
  • Carbonic acid derivative
  • Oxacycle
  • Azacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point226 °C (mesylate salt)Not Available
Boiling PointNot AvailableNot Available
Water Solubility0.015 g/LNot Available
LogP3Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM214.630932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.015 g/LALOGPS
logP3.47ALOGPS
logP4.38ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)8.27ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area86.28 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity148.93 m³·mol⁻¹ChemAxon
Polarizability55.54 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+223.41531661259
DarkChem[M-H]-219.19131661259
DeepCCS[M+H]+218.29830932474
DeepCCS[M-H]-215.90230932474
DeepCCS[M-2H]-248.78630932474
DeepCCS[M+Na]+224.21130932474
AllCCS[M+H]+224.132859911
AllCCS[M+H-H2O]+222.332859911
AllCCS[M+NH4]+225.832859911
AllCCS[M+Na]+226.332859911
AllCCS[M-H]-212.932859911
AllCCS[M+Na-2H]-213.832859911
AllCCS[M+HCOO]-215.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ImatinibCN1CCN(CC2=CC=C(C=C2)C(=O)NC2=CC(NC3=NC=CC(=N3)C3=CN=CC=C3)=C(C)C=C2)CC15474.1Standard polar33892256
ImatinibCN1CCN(CC2=CC=C(C=C2)C(=O)NC2=CC(NC3=NC=CC(=N3)C3=CN=CC=C3)=C(C)C=C2)CC14494.6Standard non polar33892256
ImatinibCN1CCN(CC2=CC=C(C=C2)C(=O)NC2=CC(NC3=NC=CC(=N3)C3=CN=CC=C3)=C(C)C=C2)CC15034.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Imatinib,1TMS,isomer #1CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)[Si](C)(C)C)C=C1NC1=NC=CC(C2=CC=CN=C2)=N14439.7Semi standard non polar33892256
Imatinib,1TMS,isomer #1CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)[Si](C)(C)C)C=C1NC1=NC=CC(C2=CC=CN=C2)=N12643.1Standard non polar33892256
Imatinib,1TMS,isomer #1CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)[Si](C)(C)C)C=C1NC1=NC=CC(C2=CC=CN=C2)=N15873.1Standard polar33892256
Imatinib,1TMS,isomer #2CC1=CC=C(NC(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C4540.1Semi standard non polar33892256
Imatinib,1TMS,isomer #2CC1=CC=C(NC(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C2926.8Standard non polar33892256
Imatinib,1TMS,isomer #2CC1=CC=C(NC(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C5795.6Standard polar33892256
Imatinib,2TMS,isomer #1CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)[Si](C)(C)C)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C4272.2Semi standard non polar33892256
Imatinib,2TMS,isomer #1CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)[Si](C)(C)C)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C2829.6Standard non polar33892256
Imatinib,2TMS,isomer #1CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)[Si](C)(C)C)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C5475.5Standard polar33892256
Imatinib,1TBDMS,isomer #1CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)[Si](C)(C)C(C)(C)C)C=C1NC1=NC=CC(C2=CC=CN=C2)=N14604.1Semi standard non polar33892256
Imatinib,1TBDMS,isomer #1CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)[Si](C)(C)C(C)(C)C)C=C1NC1=NC=CC(C2=CC=CN=C2)=N12843.4Standard non polar33892256
Imatinib,1TBDMS,isomer #1CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)[Si](C)(C)C(C)(C)C)C=C1NC1=NC=CC(C2=CC=CN=C2)=N15915.7Standard polar33892256
Imatinib,1TBDMS,isomer #2CC1=CC=C(NC(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C(C)(C)C4693.6Semi standard non polar33892256
Imatinib,1TBDMS,isomer #2CC1=CC=C(NC(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C(C)(C)C3126.6Standard non polar33892256
Imatinib,1TBDMS,isomer #2CC1=CC=C(NC(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C(C)(C)C5815.5Standard polar33892256
Imatinib,2TBDMS,isomer #1CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)[Si](C)(C)C(C)(C)C)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C(C)(C)C4603.2Semi standard non polar33892256
Imatinib,2TBDMS,isomer #1CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)[Si](C)(C)C(C)(C)C)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C(C)(C)C3324.7Standard non polar33892256
Imatinib,2TBDMS,isomer #1CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)[Si](C)(C)C(C)(C)C)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C(C)(C)C5509.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Imatinib GC-MS (Non-derivatized) - 70eV, Positivesplash10-01bd-9863300000-bf69c843c9ad9179bcdb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Imatinib GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Imatinib LC-ESI-qTof , Positive-QTOFsplash10-0006-0036900000-e06abe669a9b1b57e2c32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imatinib LC-ESI-QFT , negative-QTOFsplash10-0006-0000900000-3974d719909aa7a750392017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imatinib LC-ESI-QFT , negative-QTOFsplash10-0006-0000900000-dd386ae17930da36c11f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imatinib LC-ESI-QFT , negative-QTOFsplash10-0f6x-0159500000-576f293e026deaa1ec7f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imatinib LC-ESI-QFT , negative-QTOFsplash10-0ik9-0495000000-06102c4afd3c2e88cf872017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imatinib LC-ESI-QFT , negative-QTOFsplash10-03ka-0971000000-b487f693e17cba198e372017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imatinib LC-ESI-QFT , negative-QTOFsplash10-05fs-0930000000-9319811c561fd5cc8f2f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imatinib LC-ESI-QFT , negative-QTOFsplash10-0159-4910000000-25480eb9451aee843c262017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imatinib LC-ESI-QFT , negative-QTOFsplash10-014i-9000000000-0638bee21655c0e0ca002017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imatinib LC-ESI-QFT , negative-QTOFsplash10-014i-9000000000-76f9b62b017fe8241e672017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imatinib LC-ESI-QFT , positive-QTOFsplash10-0006-0000900000-9825e12c65f9bf36d72f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imatinib LC-ESI-QFT , positive-QTOFsplash10-0006-1029200000-acd76280414e767f02802017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imatinib LC-ESI-QFT , positive-QTOFsplash10-0006-2269000000-f55e5c707c9de5ba2d0f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imatinib LC-ESI-QFT , positive-QTOFsplash10-00ba-3494000000-19e7d8361f050ec8b6372017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imatinib LC-ESI-QFT , positive-QTOFsplash10-00ba-3693000000-c1e011113081e3341bba2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imatinib LC-ESI-QFT , positive-QTOFsplash10-0596-5981000000-a0f689cd067d45644bcd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imatinib LC-ESI-QFT , positive-QTOFsplash10-0f9f-5930000000-71f05e812cf29e11cc692017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imatinib LC-ESI-QFT , positive-QTOFsplash10-00ku-5910000000-3f91ea6a6f7402767a782017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Imatinib LC-ESI-QFT , positive-QTOFsplash10-029i-7900000000-507c771376ea4b799b6d2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imatinib 10V, Positive-QTOFsplash10-0006-0144900000-2c1268fe741d4e07f7a42016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imatinib 20V, Positive-QTOFsplash10-00kf-0698300000-b23d90ff38472b542f792016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imatinib 40V, Positive-QTOFsplash10-02tc-3911000000-88d44a81ccb6cf024cbc2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imatinib 10V, Negative-QTOFsplash10-0006-1110900000-e7ed25c6dc02f44eff1e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imatinib 20V, Negative-QTOFsplash10-002g-7534900000-56f8e35b9d7416fcc95f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Imatinib 40V, Negative-QTOFsplash10-0006-9610100000-772d808632d87b2ad3e52016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00619 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00619 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00619
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5101
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkImatinib
METLIN IDNot Available
PubChem Compound5291
PDB IDSTI
ChEBI ID45783
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Droogendijk HJ, Kluin-Nelemans HJ, van Doormaal JJ, Oranje AP, van de Loosdrecht AA, van Daele PL: Imatinib mesylate in the treatment of systemic mastocytosis: a phase II trial. Cancer. 2006 Jul 15;107(2):345-51. [PubMed:16779792 ]
  2. Vigneri P, Wang JY: Induction of apoptosis in chronic myelogenous leukemia cells through nuclear entrapment of BCR-ABL tyrosine kinase. Nat Med. 2001 Feb;7(2):228-34. [PubMed:11175855 ]
  3. Deininger MW, Druker BJ: Specific targeted therapy of chronic myelogenous leukemia with imatinib. Pharmacol Rev. 2003 Sep;55(3):401-23. Epub 2003 Jul 17. [PubMed:12869662 ]
  4. Lassila M, Allen TJ, Cao Z, Thallas V, Jandeleit-Dahm KA, Candido R, Cooper ME: Imatinib attenuates diabetes-associated atherosclerosis. Arterioscler Thromb Vasc Biol. 2004 May;24(5):935-42. Epub 2004 Feb 26. [PubMed:14988091 ]
  5. Reeves PM, Bommarius B, Lebeis S, McNulty S, Christensen J, Swimm A, Chahroudi A, Chavan R, Feinberg MB, Veach D, Bornmann W, Sherman M, Kalman D: Disabling poxvirus pathogenesis by inhibition of Abl-family tyrosine kinases. Nat Med. 2005 Jul;11(7):731-9. Epub 2005 Jun 26. [PubMed:15980865 ]